EP0154837B1 - Cosmetic emulsion and method for making the same - Google Patents

Cosmetic emulsion and method for making the same Download PDF

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Publication number
EP0154837B1
EP0154837B1 EP85101708A EP85101708A EP0154837B1 EP 0154837 B1 EP0154837 B1 EP 0154837B1 EP 85101708 A EP85101708 A EP 85101708A EP 85101708 A EP85101708 A EP 85101708A EP 0154837 B1 EP0154837 B1 EP 0154837B1
Authority
EP
European Patent Office
Prior art keywords
integer
emulsion
ethyl alcohol
oil
aqueous solution
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP85101708A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0154837A3 (en
EP0154837A2 (en
Inventor
Toshiyuki Susuki
Akira Tsukada
Masanobu Kai
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
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Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Publication of EP0154837A2 publication Critical patent/EP0154837A2/en
Publication of EP0154837A3 publication Critical patent/EP0154837A3/en
Application granted granted Critical
Publication of EP0154837B1 publication Critical patent/EP0154837B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/062Oil-in-water emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/342Alcohols having more than seven atoms in an unbroken chain
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/891Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol

Definitions

  • This invention relates to stable, low viscosity cosmetic emulsions which have the skin refreshed upon application thereof without becoming sticky after the application and which have appropriate moisture retentivity.
  • the invention also relates to a method for making such emulsions.
  • cosmetic emulsions consist of water, oils and emulsifiers and, when applied to the skin, they form an oil film on the surface of the skin. By the coverage with the oil film, a percutaneous water loss is so suppressed that moisture in the horny layer is appropriately retained.
  • the moisture-retentive effect depends on the type and amount of the oil, and thus the type and amount of the oil are suitably controlled according to the purposes.
  • EP-A-0076146 describes skin conditioning compositions which comprise an emulsion of volatile, water-insoluble liquid; glycerine; a polydiorganosiloxane-polyoxyalkylene copolymer; a surfactant which will emulsify the above named water-insoluble components; and water.
  • US-A-4311695 discloses water-in-oil type emulsions, wherein the water phase comprises a water-soluble alcohol and the oil phase comprises a methyl siloxane fluid.
  • GB-A-2064363 discloses silicone-water emulsions of volatile cyclic polysiloxanes which are suitable as vehicles for the application of epidermal enhancing agents including cosmetics and medical and pharmaceutical compounds.
  • silicone oil The polysiloxane of the general formula (II), (III) or (IV) indicated hereinafter (hereinafter referred to silicone oil) is able to form a uniform thin film on the skin and is suitable as an oil imparting the stickiness-free smoothness to the touch.
  • silicone oil is rather poor in compatibility with ordinary surface active agents and other oils and has very poor ability of being emulsified, which makes it very difficult to obtain uniform, fine emulsions.
  • the cosmetic system is preferred to contain ethyl alcohol.
  • ethyl alcohol In general, addition of ethyl alcohol results in a considerable lowering of emulsion stability of the system.
  • the emulsion system having such properties as described above should satisfy the following requirements: ethyl alcohol is contained in an aqueous phase; an oil being emulsified is mainly composed of silicone oil and is contained in small amounts; and the system is low in viscosity and has emulsified particles which are fine and uniform in size.
  • known emulsification techniques cannot satisfy all the above requirements at the same time.
  • the present inventors have made intensive studies to obtain cosmetic emulsions for which the objects of the invention can be achieved.
  • a mixture of a specific type of dimethylpolysiloxane-polyoxyalkylene copolymer, a surface active agent having an HLB value not smaller than 10, and a linear, saturated higher alcohol having from 12 to 22 carbon atoms is used as an emulsifier, to which an aqueous phase comprising ethyl alcohol in a predetermined concentration is added under agitation in a predetermined range of temperature thereby forming one phase region of a gel or a highly viscous liquid, there can be obtained an emulsion with a low viscosity which is fine, uniform and stable and which contains the silicone oil as the main component.
  • the emulsion composition satisfies the requirements for the cosmetic emulsion.
  • the present invention is based on the above finding.
  • a cosmetic emulsion which comprises:
  • Another feature of the invention resides in provision of a method of making the cosmetic emulsion.
  • the sole figure is a ternary composition diagram showing relative ratios of dimethylpolysiloxane-polyoxyalkylene copolymer, a surface active agent having an HLB value not smaller than 10, and a linear, saturated higher alcohol having 12 to 22 carbon atoms, which constitute an emulsifier of a cosmetic emulsion of the invention.
  • the dimethylpolysiloxane-polyoxyalkylene copolymer of (1) which is one component of the emulsifier (a) of the cosmetic emulsion according to the invention, should preferably have a cloud point, as an aqueous solution thereof, of 25 to 40°C. If the cloud point of the aqueous solution exceeds 45°C, one phase emulsion cannot be formed during the emulsification and the emulsified particles of the emulsion become coarse. On the other hand, when the cloud point is lower than 20°C, it does by no means serve as a surface active agent and thus no emulsification proceeds.
  • the surface active agent (2) are those agents having an HLB value not smaller than 10, which may be used singly or in combination.
  • surface active agents having an HLB value of from 11 to 16 are preferred.
  • Specific examples of the surface active agents include polyoxyethylene alkyl ethers, polyoxyethylene and fatty acid esters, fatty acid esters of polyoxyethylene and sorbitan, fatty acid esters of polyoxyethylene and glycerine, polyoxyethylene hardened castor oils, polyglycerine and fatty acid esters, sucrose and fatty acid esters.
  • the linear, saturated higher alcohols (3) have from 12 to 22 carbon atoms, preferably 14 to 18 carbon atoms.
  • the action of stabilizing a material being emulsified lowers to a substantial extent with offensive odor.
  • the number of carbon atoms exceeds 22, there is the tendency toward crystallization as time passes.
  • the emulsifier which is component (a) has relative ratios of (1), (2) and (3) within a polygon (including each side thereof) bounded by the points A(25: 73: 2), B(25: 55: 20), C(70: 10: 20) and D(88: 10: 2) of the ternary composition diagram of the sole figure.
  • the emulsifier is used in an amount of 0.2 to 5 wt% (hereinafter referred to simply as %) of the cosmetic emulsion and preferably in an amount of 0.4 to 3%. Outside the range, the emulsification does not proceed satisfactorily.
  • the oil component (b) contains 90% or more of at least one silicone oil represented by the general formula (II), (III) or (IV).
  • silicone oils there may be used hydrocarbons such as liquid paraffin, paraffin wax, ceresin and squalane, natural animal and plant oils such as olive oil, jojoba oil and mink oil, and synthetic ester oils such as octyldodecyl myristate. These oils are used in an amount of 0.5 to 10%, preferably 1 to 5%, of the cosmetic emulsion. Over 10%, oiliness is unfavorably strengthened.
  • the aqueous phase (c) should have a ratio by weight of ethyl alcohol and water in the range of 50/50 to 2/98.
  • the ratio is preferably in the range of 30/70 to 5/95.
  • the ethyl alcohol/water ratio exceeds 50/50, the emulsification becomes unstable and the resulting emulsion is more stimulative against the skin. If, on the contrary, the ratio of ethyl alcohol/water is smaller than 2/98, refreshness does not appear.
  • the aqueous phase may further comprise humectants such as glycerin, sorbitol, maltitol propylene glycol, dipropylene glycol, 1,3-butylene glycol, sodium pyrrolidonecarboxylate, polyoxyethylene methylglucoside, polyoxypropylene methylglucoside and glucose, amino acids such as glycine, serine and proline, and medical agents such as antiinflammatory agents, bactericides and vitamins.
  • the aqueous phase is used in an amount of 85 to 99.3%, preferably 92 to 98.6%, of the cosmetic emulsion.
  • the cosmetic emulsion of the invention is preferred to be low in viscosity and has generally a viscosity of below 100 mPa ⁇ s (cP) at 25°C, preferably below 20 mPa ⁇ s (cP). Over 100 mPa ⁇ s (cP), the resulting emulsion is felt sticky upon application thereof.
  • the cosmetic emulsion of the invention is prepared by the procedure which comprises adding an ethyl alcohol aqueous solution, which has an ethyl alcohol/water ratio by weight of 20/80 to 70/30, to a mixture of (a) 0.2 to 5 parts by weight of an emulsifier and (b) 0.5 to 10 parts by weight of an oil under agitation at a temperature of from 20 to 45°C to produce an o/w emulsion, and, if necessary, further adding water or an ethyl alcohol aqueous solution to give an intended composition.
  • ethyl alcohol aqueous solution having an ethyl alcohol/water ratio by weight of 20/80 to 70/30, preferably 30/70 to 60/40 is added in an amount of 0.5 to 5 times by weight the mixture of (a) and (b), a gel-like or highly viscous liquid one phase product is produced. Further addition of ethyl alcohol results in an o/w emulsion. If necessary, water or an ethyl alcohol aqueous solution is so added that the ratio by weight of ethyl alcohol/water is in the range of 50/50 to 2/98. The finally added water or ethyl alcohol aqueous solution should preferably be controlled at a temperature of from 5 to 45°C.
  • One of features of the invention resides in that one phase region is formed by emulsification using a high content of ethanol, through which region uniform and fine emulsified particles are obtained.
  • the fact that fine emulsified particles are obtained through the one phase region during the course of the emulsification is known per se with regard to ordinary oil/emulsifier/water systems and oil/emulsifier/water/dihydric alcohol systems ("Journal of Chemical Society of Japan, 10, 1399 (1983), by Sagitani).
  • the method for making cosmetic emulsions according to the invention is different from these known methods in that one phase region is formed under conditions of a high ethyl alcohol concentration in the system comprising an oil chiefly made of silicone oil, thereby obtaining a stable, low viscosity emulsion composition comprising fine, uniform emulsified particles.
  • a high ethyl alcohol concentration in the system comprising an oil chiefly made of silicone oil, thereby obtaining a stable, low viscosity emulsion composition comprising fine, uniform emulsified particles.
  • Japanese Laid-open Patent Application No. 58-131910 that polydiorganosiloxane-polyoxyalkylene copolymers are effective for emulsifying silicone oils.
  • the present invention is also different from this prior art in that the emulsifier useful in the present invention consists of dimethylpolysiloxane-polyoxyalkylene copolymer, a surface active agent having an HLB value not smaller than 10, and a linear, saturated higher alcohol having from 12 to 22 carbon atoms in specific ratios, that an aqueous solution of the dimethylpolysiloxane-polyoxyalkylene copolymer has such a low cloud point of from 20 to 45°C that it does not serve as an emulsifier under ordinary emulsifying conditions, but shows good performance as the emulsifier by defining the content of ethyl alcohol and the emulsification temperature in certain ranges, respectively.
  • Emulsion compositions of the formulations indicated in Table 3 were prepared to check the emulsion stability and viscosity. The results are shown in Table 4. The preparation of each emulsion was made in the same manner as in Example 1.
  • Example 5 Five samples, in total, including the cosmetic emulsions A obtained in Example 1 and the cosmetic emulsion I of Example 2, both of which were the products of the invention, and the comparative emulsions J, K and O of Example 2 were organoleptically evaluated by 10 expert panelers with regard to the feelings to the touch. The results are shown in Table 5 below.
  • the products of the invention are better in refreshness, less in stickiness and oiliness, and better in affinity for skin and appearance than the comparative products.
  • Emulsion compositions P, Q of the invention having formulations indicated in Table 6, a comparative product R free of any oils, and commercially sold lotion S were each applied onto the flexor side of the forearm of men, followed by measurement of a skin conductance.
  • the skin conductance corresponds to a content of water in the epidermic corneum, meaning a greater amount of water at a higher conductance value.
  • the measurement was effected using a high frequency impedance meter (Capacitance-conductance Meter Model 354, by IBS Co., Ltd.). The results are shown in Table 7 below.
  • the comparative product R was a transparent liquid, not an emulsion.
  • the cosmetic emulsions of the invention show a higher skin moisture-retentive effect than the comparative product R and the commercial lotion.
  • Example 1 The cosmetic emulsion A obtained in Example 1 which is a product of the invention was used but prepare in different manners to determine the state and stability of the resulting emulsions.
  • the preparatory procedures are summarized in Table 8 with the results shown in Table 9 below.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP85101708A 1984-03-16 1985-02-15 Cosmetic emulsion and method for making the same Expired - Lifetime EP0154837B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP50547/84 1984-03-16
JP59050547A JPS60197610A (ja) 1984-03-16 1984-03-16 乳化化粧料およびその製造法

Publications (3)

Publication Number Publication Date
EP0154837A2 EP0154837A2 (en) 1985-09-18
EP0154837A3 EP0154837A3 (en) 1987-05-06
EP0154837B1 true EP0154837B1 (en) 1992-08-05

Family

ID=12862032

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85101708A Expired - Lifetime EP0154837B1 (en) 1984-03-16 1985-02-15 Cosmetic emulsion and method for making the same

Country Status (10)

Country Link
US (1) US4675179A (sv)
EP (1) EP0154837B1 (sv)
JP (1) JPS60197610A (sv)
KR (1) KR910003553B1 (sv)
DE (2) DE3586436D1 (sv)
ES (1) ES8705220A1 (sv)
HK (1) HK109193A (sv)
MX (1) MX161337A (sv)
MY (1) MY100353A (sv)
PH (1) PH21380A (sv)

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USRE34584E (en) 1984-11-09 1994-04-12 The Procter & Gamble Company Shampoo compositions
JPH0678217B2 (ja) * 1986-09-18 1994-10-05 花王株式会社 乳化型毛髪化粧料
CA1328813C (en) * 1986-11-06 1994-04-26 Hiroshi Tanaka Skin irritation alleviation agent and composition thereof
US5066485A (en) * 1987-02-06 1991-11-19 Revlon, Inc. Cosmetic compositions comprising oil-in-water emulsion containing pigment
JP2622980B2 (ja) * 1987-02-06 1997-06-25 レブロン・コンシューマー・プロダクツ・コーポレーション 顔料を含有する水中油型エマルションから成る化粧用組成物
JPS63250311A (ja) * 1987-04-06 1988-10-18 Kao Corp 油中水型化粧料
GB8714658D0 (en) * 1987-06-23 1987-07-29 Boots Co Plc Cosmetic composition
JP2691729B2 (ja) * 1987-06-23 1997-12-17 株式会社資生堂 固型状油中水型乳化化粧料
US4835002A (en) * 1987-07-10 1989-05-30 Wolf Peter A Microemulsions of oil in water and alcohol
JPH01155982A (ja) * 1987-12-11 1989-06-19 Agency Of Ind Science & Technol 管内の閉塞物除去装置
US5036108A (en) * 1988-12-14 1991-07-30 Kao Corporation Water-in-oil emulsion cosmetic
DE69020211T2 (de) * 1989-04-05 1995-11-02 Kao Corp Kosmetische Doppelemulsionszusammensetzung.
GB8914905D0 (en) * 1989-06-29 1989-08-23 Unilever Plc Cosmetic composition
US5439677A (en) * 1989-07-24 1995-08-08 The Dial Corp. Compositions and methods for treating hair using a mixture of polysiloxanes
FR2676921B1 (fr) * 1991-05-27 1995-04-14 Oreal Emulsion stable du type huile-dans-eau a base d'huile de silicone et son utilisation en cosmetique et en dermatologie.
JPH05112440A (ja) * 1991-08-09 1993-05-07 Sayuri Takemoto 消臭用塗布剤
FR2683453B1 (fr) * 1991-11-07 1994-04-08 Saint Laurent Parfums Yves Emulsion cosmetique translucide eau dans silicone, enrichie en principes actifs.
DE4206732A1 (de) * 1992-03-04 1993-09-09 Goldschmidt Ag Th Fluessige, lagerstabile, multiple emulsion des typs o/w/o
DE4343833A1 (de) * 1993-12-22 1995-06-29 Beiersdorf Ag W/O/W-Emulsionen
EP0782882B1 (en) * 1995-07-12 2002-12-04 Shiseido Company Limited Oil-in-alcohol emulsion composition
US5916543A (en) * 1996-12-18 1999-06-29 Schering-Plough Healthcare Products, Inc. Emulsions having minimal rub-in times
EP0970741B1 (en) * 1997-07-17 2008-05-14 Shiseido Company Limited O/w/o type multiphase emulsion
ES2242661T3 (es) 2000-02-19 2005-11-16 Goldschmidt Gmbh Emulsiones de aceite en agua cosmeticas y farmaceuticas de polisiloxanos modificados con poliesteres.
US20030040571A1 (en) * 2001-07-30 2003-02-27 Feng Qian Jane Clear silicone microemulsions formed spontaneously
DE10234883A1 (de) * 2002-07-31 2004-02-19 Beiersdorf Ag Kosmetische und/oder dermatologische Zubereitung
DE10234885B4 (de) * 2002-07-31 2005-03-10 Beiersdorf Ag Kosmetische und/oder dermatologische Silikon-in Wasser-Emulsionen und transparentes Packmittel enthaltend diese Sonnenschutzzubereitungen
TW200413018A (en) * 2002-12-26 2004-08-01 Shiseido Co Ltd Oil-in-water type emulsified cosmetic
JP2012072085A (ja) * 2010-09-29 2012-04-12 Shiseido Co Ltd 水中油型乳化化粧料
JP6730241B2 (ja) * 2017-10-04 2020-07-29 花王株式会社 スキンケア方法

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Also Published As

Publication number Publication date
HK109193A (en) 1993-10-22
MY100353A (en) 1990-08-28
DE3586436T4 (de) 1993-10-07
JPS625881B2 (sv) 1987-02-07
ES541053A0 (es) 1987-05-01
ES8705220A1 (es) 1987-05-01
JPS60197610A (ja) 1985-10-07
EP0154837A3 (en) 1987-05-06
EP0154837A2 (en) 1985-09-18
DE3586436D1 (de) 1992-09-10
US4675179A (en) 1987-06-23
DE3586436T2 (de) 1993-02-11
KR910003553B1 (ko) 1991-06-05
KR850006321A (ko) 1985-10-05
MX161337A (es) 1990-09-10
PH21380A (en) 1987-10-15

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